title: Taming of a superbase for selective phenol desilylation and natural product isolation.
abstract: Hydroxyl moieties are highly prevalent in natural products. We previously reported a chemoselective strategy for enrichment of hydroxyl-functionalized molecules by formation of a silyl ether bond to a resin. To generate smaller pools of molecules for analysis, we developed cleavage conditions to promote stepwise release of phenolic silyl ethers followed by aliphatic silyl ethers with a "tamed" version of the superbase 1,1,3,3-tetramethylguanadine. We demonstrate this as a general strategy for selective deprotection of phenolic silyl ethers under neutral conditions at room temperature.
authors.affiliation: Department of Chemistry, Indiana University, 212 South Hawthorne Drive, Bloomington, Indiana 47405, United States.
authors.forename: Darci J
authors.initials: DJ
authors.lastname: Trader
authors.forename: Erin E
authors.initials: EE
authors.lastname: Carlson
mesh_terms: D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification*; D006146:Guanidines / Q000737:chemistry*; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013696:Temperature
chemical_list: D001688:Biological Products; D006146:Guanidines; D017646:Organosilicon Compounds; D010636:Phenols; C477069:1,1,3,3-tetramethylguanidine